Hydrochloric Acid → HCID 86715505, compound

HRID 2284594Notes

Reaction equation

HRID 2284594 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:22].Cl>CCO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[N:16][C:17]([CH2:20][NH2:21])=[CH:18][CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86715506HCID 86715506, compound

Product 1

HCID 86715505HCID 86715505, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2′-(4-Fluoro-3-methylphenyl)-[3,3′-bipyridine]-6-carbonitrile (2.2 g), Pd/C (0.4 g) and conc. HCl (3 mL) in EtOH (100 mL) was hydrogenated in a par shaker at 40 psi overnight. The reaction mixture was filtered through Celite® and concentrated. The concentrate was treated with CH2Cl2 (120 mL) and sat. aq. NaHCO3 (25 mL). Organic layer was separated and the aqueous layer was re-extracted with CH2Cl2 (2×50 ml). Combined organic layers were stirred over anhydrous Na2SO4 for 30 min, filtered, concentrated and dried under high vacuum to obtain thick viscous liquid of (2′-(4-Fluoro-3-methylphenyl)-[3,3′-bipyridin]-6-yl)methanamine (2.1 g, purity 97%). 1H NMR (300 MHz, DMSO-d6): δ 8.66 (dd, J=4.7, 1.6 Hz, 1H), 8.26 (s, 1H), 7.86 (d, J=1.6 Hz, 1H), 7.54 (dd, J=8.0, 2.2 Hz, 1H), 7.48 (dd, J=7.7, 4.8 Hz, 1H), 7.37 (d, J=8.1 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 6.97 (dd, J=6.9, 1.5 Hz, 2H), 3.78 (s, 2H), 2.58 (br s, 2H), 2.16 (s, 3H).

Workup

  1. customwas hydrogenated in a par shaker at 40 psi overnight
  2. filtrationThe reaction mixture was filtered through Celite®
  3. concentrationconcentrated
  4. additionThe concentrate was treated with CH2Cl2 (120 mL) and sat. aq. NaHCO3 (25 mL)
  5. customOrganic layer was separated
  6. extractionthe aqueous layer was re-extracted with CH2Cl2 (2×50 ml)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-ec9ff9f6a4664a74becad63101002980
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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